The scariest part of anybody’s travel is the planning stage. It can also be the most exciting, but oftentimes just thinking about everything that needs to be done before a trip is the most daunting and overwhelming part.

The scariest part of anybody’s travel is the planning stage. It can also be the most exciting, but oftentimes just thinking about everything that needs to be done before a trip is the most daunting and overwhelming part.

I’m a big proponent for the “just wing it” style of travel. Sometimes it costs an extra dollar or two, but it means that I don’t have to plan anything, which leaves the potential for my journeys wide open. When I have a plan, it means that everything must go according to it. Without one, anything is possible. The stories are always better and, somehow, things always work out.

I arrived in Colombia two weeks ago and, though I had some rough ideas about what I would do and where I would go, the only thing I had planned was my first night’s accommodation. People usually look at me like I’m crazy, but I always just grin and nod.

Having done this more than a few times, it’s definitely my preferred approach. I try not to stress about planning things, specifically my itinerary. People ask what my plans are, and the answer is almost universally, “I don’t have a clue.”

There are, however, a number of ways to make the planning stage of your travels easier. Though I don’t map out much of my itinerary, the planning stages are actually the most important. When it comes to things like insurance, vaccinations, visas and documentation, packing, and financial planning, it’s really important to make sure everything is in order.

I’ve compiled my best tips for the planning stage of your travels and reached out to some other bloggers for some insight.

1. Check Your Destination’s Exit Requirements

I came to Colombia with a one-way ticket. The airlines, however, do not allow this, because if I were to get stuck in Colombia or deported for overstaying my visa, they’re the ones who’d have to pay my way out. I do plan on leaving before my visa expires, I just didn’t have my ticket purchased yet. But without one, I wasn’t going to be allowed into the country.

Along with your ticket, passport, and carry-on, make sure you have some means by which to prove that you have plans to exit the country you’re traveling to. Whether it be by bus, boat, or plane, having a ticket out – even a refundable one – can save you hours of questioning and even the cost of the last minute air fare you could find yourself buying at check-in. If the airline doesn’t see proof of onward travel, you may not be allowed to board your flight.

All airlines must offer refunds within 24 hours of booking, so you can book a return ticket before you take off and cancel it once you land. If you’re using a flight aggregator, like Orbitz or Kayak, you may or may not be eligible for a refund, so just make sure the flight you book is refundable—they usually make it pretty obvious.

Sunrise in Tayrona National Park, Colombia

2. Backup All Your Documentation

In case anything goes wrong (fingers crossed that it doesn’t), it’s imperative to have all your documentation backed up somewhere online. A copy of your passport could help to prove your identity in a pinch or, if your credit card goes missing, you’ll still be able to make purchases online with the card number.

“Before you leave home, be sure to use the internet's “cloud” to your advantage. Having copies of your passport, credit card, insurance and tickets available on your smartphone or (in a worst case scenario) via an internet cafe can be priceless. It's also a great place to store images you take during the trip in case of theft or equipment failure.”

I recommend Dropbox for those using a Mac or Google Drive for those using Windows. If you want to backup your entire laptop to the cloud (which I do recommend, whether you’re traveling or not), my personal favorite is Backblaze. I’ve been a happy customer of theirs for 6+ years now.

Boarding a bamboo boat on the Li River in Guilin, China

3. Get Travel Insurance. Seriously.

I’ve been in situations where I didn’t need it and I didn’t have it, and I’ve been in situations where I really needed it and I’m very glad that I had it. After further adventures, what I’ve realized is that, especially on your travels, anything can happen, and you’re always better off being covered. It could mean a couple hundred bucks now or a couple hundred thousand later.

I've always found World Nomads to have the best coverage at the best price.

Always read the fine print on your travel insurance policy to find out the dollar amount of your coverage maximum, and make sure this is enough to cover you in a serious medical emergency at your destination. Some policies have relatively low limits for maximum coverage that are quickly exhausted if something major happens to you and you could end up being on the hook for hundreds of thousands of dollars in costs.

Also make sure that what you’re getting is actually travel insurance, not just health insurance. Travel insurance covers things like loss or damage to personal effects and trip cancellations as well as health insurance and emergency evacuation coverage.

Beach on the island of Vieques, Puerto Rico

4. Create a City Guide Before You Arrive

The most disorienting moment is when you first arrive in a city after you get your bags dropped off at your accommodation, and you walk out the front door.

Create a basic guide of the city and put pins on every place on a map, so you can enjoy the neighborhood seeing everything you want around it. But always leave lots of space to wander around and get lost. This is usually the best way to find cool and unique stuff, creating an experience that is totally yours that a guide could never give to you.

Google Maps is the perfect app for your smartphone. After researching all the notable spots that you want to visit, type them into Google Maps and click “Save,” which will add a star to your map. Then you can see which areas have the highest concentration of places that you want to go. If you have a Google account, this will also sync across devices, meaning you can star the items on the web interface and they will show up on your mobile.

Colorful streets of Cartagena, Colombia

5. Get Vaccinated and Keep the Records

Every country requires different vaccinations, and some won’t let you enter without proof. When I entered China, I went through a rigorous medical procedure full of tests, shots, and ultrasounds. If I actually had some of my previous records on hand, I probably could have avoided a major headache.

Make sure you keep comprehensive copies of all vaccination records. Treat your doctor's certificates and documents with the same security as your passport, and keep electronic copies, along with details of the clinic and doctor you saw for future reference. The worst thing in the world is realizing you need a yellow fever certificate for to travel to South America, and having lost proof of being given the horrific $300 shot 4 years ago for an Africa trip. Luckily, your clinic will generally have records of your shots, and in most instances will be able to re-issue certificates for a fee.

If you’re not keen on carrying all this information around, scan everything and keep it backed up somewhere online, like Travis recommended. You’ll only need it once in a while, so carrying the actual documents isn’t entirely necessary.

Trekking in the mountains of Sapa in Northern Vietnam

6. Double Check Your Visa Requirements

I've never had an issue, but I've seen it happen. A close friend of mine thought she could get a visa on arrival, and just four days before she was supposed to leave, she learned that the visa application process took at least two weeks. She made some phone calls and frantically got her passport delivered, with visa and all, the same day she was leaving for her flight. Talk about stress.

Make use of travel discussion boards or Facebook groups to get up to date information from people who have visited recently, or go straight to the horse’s mouth and ask an embassy/consulate. In some countries, it absolutely pays to arrange your visa beforehand, but in others, it might be quick and easy to handle it upon arrival. In Tanzania, I pre-purchased my visa and waited twice as long as my travel companion who showed up and bought one at the border.

And when it comes to visa runs, do your research as to how manageable they are and if there are any scams you should be aware of. I found it much easier to shell out a little extra to avoid the Thailand-Cambodia border crossing after hearing so many unpleasant things about it.

Longtail boats in Thailand

7. Read the Fine Print on Everything

Anything that’s important, that is. That 58 page iTunes disclaimer is not getting read, but if it’s a plane ticket, your travel insurance, a bus booking, or anything else that has to do with the actual travel or financial portion of your trip, read it!

No one likes fine print, but if you are traveling by air, it is essential to read it when trip planning. Otherwise, you can really risk blowing your budget with ridiculous airline fees dominating the air travel industry these days. Need to print your boarding pass at the airport? Some airlines charge for that (like Ryanair). Bringing a bag between 40-50 pounds? That can incur an oversized bag fee on some airlines. Be sure to total up all the fees that might affect you before committing to an airline and booking your ticket.

8. Don't Forget Your ESTA

As a US citizen, I have absolutely no experience with visas in the United States, but whether you're actually spending time on the ground or just passing through, read up on the ESTA Visa and apply to find out if you're eligible for the Visa Waiver Program.

If you are a non-US citizen (excluding Canadians), remember to get an ESTA (Electronic System for Travel Authorization) Visa to visit the US. It’s an online system that tells you if you are eligible to travel to the US under the Visa Waiver Program. You must fill the form even if you are passing through and in transit. The ESTA Visa lasts 2 years and cannot be renewed. You can only reapply. Remember to have a copy with you when you go to the US.

9. Consider Every Item in Your Bag

Every item you carry is extra weight in your bag, and you don't want to carry stuff you don’t use or never need. Even other seasoned travelers look at me funny when I tell them that I only own one pair of pants (it’s true). The fact is, it’s all I need. I also only carry one pair of shorts.

Just because the airline allows you to take 20kg of luggage doesn’t mean that you have to take 20kg. Try to pack clothing that matches with multiple items of other clothing and shoes that can be worn for most occasions. You can wear trousers or shorts two days or more and wash smaller items in the sink or shower of your hotel. Items that are quick drying will also save you from having to carry around wet laundry. The less you carry, the easier it will be to get around and the more weight and space you will have to bring home goodies.

Pack efficiently by rolling your clothes – You'd be amazed how much space you can save simply by rolling your clothes. Although it may seem counter intuitive, the advantage of having your clothes rolled is that you can get them in a much more compact and tighter form. Folding your clothes is even more ideal in backpacks because you don't have the space to lay things flat. Furthermore, with the help of packing cubes, you can keep different types of rolled clothes together for quick access and organization.

I’ve traveled to all kinds of places in all kinds of climates with a 50-liter bag on my back and a smaller carry-on/day pack for my laptop, passport, and any other essentials. The lighter you pack, the easier it is to move, and sometimes the less you have to pay for check-in fees. In fact, given their size, I don’t even usually check my bags!

Make it a point to learn a handful of common phrases in the official language of your destination. While it's true that English is fairly ubiquitous these days, locals always appreciate the effort to communicate in their language, even if it's a simple “hello” or “thank you.” Websites like Duolingo can help you take it a step further to learn useful phrases such as “How much is it?” or “Where is the bathroom?” or “Do you have a condom?”

Download a few handy mobile apps (Duolingo and Google Translate are both free) so you can brush up while waiting to board your flight.

Landscapes in Yangshuo, China

11. Memorize Your Passport

I know every detail of my passport, including the number, date of issue, and expiration. Just make sure you actually bring it with you and don’t lose it the day before you travel. That’s what I did about 10 years ago on one of my junkets to the Dominican Republic, forcing me to forgo my entire jaunt on my way to the airport.

Before each trip always reconfirm the expiration date on your passport as various countries require you to have X amount of months left until it expires to enter. To make sure you play it safe, reference the passport guidelines for each country you are visiting and always renew your passport when there are 6 months remaining before expiration.

I think we’re all a little disorganized in some way or another. That’s why I wanted to put together this list…if it can be used to check items off before we travel, we’ll all be able to travel smarter!

The tip I appreciate the most is the one about using Duolingo to learn a little of the language before you arrive. Just a few words and knowing how to say ‘beautiful smile’ in the local language can go a long way.

Great tips Jeremy! Agreed fully on both exit tickets and visa requirements. For many trips we weren’t asked for proof of exit and then, 2 years back, I recalled a Jet Blue flight to Costa Rica. We couldn’t board the plane without proof of exiting the country so we found a WiFi hot spot at JKF in NYC and bought 2 cheap tix out of the country. Piece of cake. We were also asked a few more times, once when flying from Sydney to Bali, and again, I get the reason why.

As for visa stuff it always pays to pay extra to do it legitimately or to avoid corrupt guards. Also, do your online research to find silly little rules. For example, after doing the visa run from Chiang Mai to Myanmar about 5 times, paying in Baht, we were told we needed to pay in USD. We had the money, but in Baht. Guard wouldn’t budge. I was very nice, and conciliatory, but I simply sat in the guard house for like 15 minutes, not saying anything other than smiling, and he finally gave in. So from then on out we always had USD on us for the visa. Lesson learned.

Yeah, paying USD to enter Cambodia was really strange. I didn’t quite understand that either, but it always pays to do a little bit of research ahead of time. Exit requirements are a big one, though, especially if you’re flying one way!

Excellent set of tips, thanks for including ours! I definitely agree on memorizing your passport – I also scan mine so that I’ve got access tot he information at all times regardless of what happens – thankfully have never needed the scanned copy yet but you never know! Reconfirming the passport expiration date is also a fab tip – I had a scare last year regarding this! Will need to get a new passport within the next few months :D!

Great tips. I’m all for travel insurance. We’ve always travelled with it, but after Dave broke his back in the Amazon this year and had to be airlifted out of the Amazon to a hospital in Peru. After a week there, he was air lifted home via air ambulance and that would have cost us a fortune as well as taking a risk with his health. Travel insurance saved our bacon.

Yeah, you guys are VERY lucky you had travel insurance. I never used to have it when I traveled, but now I won’t travel without coverage. I’m so glad Dave is okay, and he definitely wouldn’t be if you didn’t have insurance.

Great list of tips. I’ve never heard of the ESTA visa before, so that mention had me a little confused and worried and panicked that maybe I didn’t know about something which could make my transits and visa issues easier… it’s only for non-Americans.

All great tips. I think people often underestimate the value of trying to speak some of the local language when they travel; it’s a great way to make friends and really does enhance the trip.

I’d like to mention two other programs as well: TSA Precheck, which expedites passing through some security lines, and Global Entry, which enables qualified people to zip through border control in a number of countries.

Hi Jeremy. Great list of tips. One that I might add is to include a sheet of heat repelling packing in your bag, in the event that you want to bring back something that is very sensitive to heat — like chocolate!

Excellent tips, Jeremy. I never thought of memorizing my passport. It would be very difficult though (please don’t look down on me for that!) I have a very bad memory. I do most of the things you list here, except buying travel insurance and I have to say that once, but only once, I regretted it. My father in law passed away unexpectedly and I had to cancel a $4000 trip on the spot, with no refund. But I still didn’t learn my lesson. I still keep pushing my luck with that. Very useful post, thank you.

Great planning tips – having the passport info memorized is key! As I’m based in Africa, the whole “on arrival” visa is never a certainty and can be a big hassle, especially for those traveling overland.

Great information from lots of people that would know. Our planning tip would be to make sure you have a hundred dollars or so in a few places as an emergency (e.g. in your backpack, suitcase and laptop bag).

Great info Jeremy, thanks. It can be daunting at times, but planning the trip feels like starting to travel already (and its nicer than to get your shots ;-))! We use Google Maps as well to create interactive maps to plan our trips and we share them afterwards so that our readers can benefit from them. And they are compatible with maps.me, a fantastic free app thanks to which we never get lost and never pay roaming fees to find our way! How to feel like a local with our interactive maps on your phone for free: short tutorial: https://bestregardsfromfar.com/2015/10/25/interactive-maps-on-the-go/

I was planning to write the same article for my blog! I mean, I chose the same topic. Most likely, now I will not do this. You already said everything 😀 Despite the fact that you left me without an idea for the next post, I still like yours 😀 Thanks for sharing tips and your personal experience with us!